#2 Christian (6 Appearances)
Christian has always been dealt a bad hand by WWE.
Christian was one-sixth of the fantastic set of TLC matches between himself and Edge, the Hardy Boyz, and the Dudleys. He was incredibly talented both in the ring and on the microphone, but was always viewed as the little brother, literally in some cases, to his tag-team partner Edge.
Edge would go on to multiple world titles, a Hall of Fame induction and becoming the winner of the first-ever Money in the Bank match. But Christian had to settle on being the guy who always delivers, but never rewarded to perhaps the level he should be.
And this has been proven with the fact he has been entrusted to appear in six Money in the Bank matches- 2005, 2009, twice in 2010, 2012 and 2013. However, he has never claimed the match in victory. Funnily enough, when you think of Christian in conjuncture with the name of the stipulation, the first thing that pops into most people's heads was his fantastic world title contest against Randy Orton at the 2011 PPV of the same name.
But despite not winning the match after six attempts, he can have comfort in the fact he is 'Mr. MITB' in terms of most appearances...with the exception of one man.